title: A versatile approach to N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitols and 1,4-dideoxy-1,4-imino-L-xylitols.
abstract: A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs and School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.
authors.forename: Guan-Nan
authors.initials: GN
authors.lastname: Wang
authors.forename: Lin
authors.initials: L
authors.lastname: Yang
authors.forename: Li-He
authors.initials: LH
authors.lastname: Zhang
authors.forename: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D000478:Alkylation; D001089:Arabinose; D050113:Imino Furanoses / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D014993:Xylitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C467078:1,4-dideoxy-1,4-imino-xylitol; D050113:Imino Furanoses; D007769:Lactams; D013402:Sugar Alcohols; C058137:1,4-dideoxy-1,4-iminoarabinitol; D001089:Arabinose; D014993:Xylitol